A number of phenol-functional organosilicon compounds and methods for their synthesis are known. For example, U.S. Pat. No. 3,622,609 teaches a method for the synthesis of 1,3-bis-.gamma.-(ortho-hydroxyphenyl)propyl- 1,1,3,3-tetramethyldisiloxane by the dimethylsilylation of the hydroxyl group in 2-allylphenol, hydrosilylation polymerization of the reaction product, and then ring opening with sodium hydroxide followed by treatment with sulfuric acid. However, this method cannot provide compounds containing both a phenol group and a functional group other than a phenol group. Japanese Laid Open (Kokai or Unexamined) Patent Application Numbers Hei 2-166123 (166,123/1990) and Hei 2-225524 (225,524/1990) describe a method for synthesizing phenol-functional organosiloxanes by carrying out an addition reaction between an SiH-functional organosiloxane and tert-butoxystyrene (phenolic hydroxyl protected by the tert-butyl group) followed by de-tert-butylation in the presence of a strong acid. This method is, however, unable to produce compounds that contain the phenol group and alkenyl in the same molecule and also suffers from the disadvantage that the siloxane chain is susceptible to cleavage by the strong acid. Otherwise, Japanese Laid Open (Kokai or Unexamined) Patent Application Numbers Sho 62-275116 (275,116/1987) and Sho 61-84022 (84,02211986) describe phenol-functional silanes, but these compounds are limited to phenol-functional trialkylsilanes and do not include alkoxysilyl-functional or silanol-functional species. Moreover, the synthetic methods disclosed therein are very complex and do not provide high yields.
The present inventors have already disclosed organosiloxanes that contain both alkenyl and the phenol group as well as a method for the synthesis thereof (Japanese Patent Application Number Hei 10-294580 (294,580/1998)). Unfortunately, this method carries with it the risk that the alkenyl group-containing organosiloxane product will polymerize during the purification phase. In addition, this method cannot be used to synthesize compounds that contain both the phenol group and alkoxysilyl group or silanol group in the same molecule.